A New Method for Generating Sn-H Bonds: Reactions of Tin Amides with Silicon Hydrides

Journal of Organic Chemistry

Volumn 62, Issue 21, 1997, Pages 7070-7071

  Hays, David S ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000281179     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9710700     Document Type: Article

References (33)

1. Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworths: Boston, 1987.
2. 3SnH, see: (a) RajanBabu, T. V. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995. (b) Neumann, W. P. Synthesis 1987, 665-683.
3. 3SnH, see: (a) RajanBabu, T. V. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995. (b) Neumann, W. P. Synthesis 1987, 665-683.
4. Boyer, I. J. Toxicology 1989, 55, 253-298.
5. 3SnH, see: Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531-2532.
6. 3SnH, see: Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531-2532.
7. 3SnH, see: Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531-2532.
8. 3SnH, see: Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531-2532.
9. 3SnH, see: Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531-2532.
10. 3SnH with borohydrides, see: Birnbaum, E. R.; Javora, P. H. J. Organomet. Chem. 1967, 9, 379-392.
11. For catalytic processes, see: (a) Corey, E. J.; Suggs, J. W. J. Org. Chem. 1975, 40, 2554-2555. (b) Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1986, 108, 303-304.
12. For catalytic processes, see: (a) Corey, E. J.; Suggs, J. W. J. Org. Chem. 1975, 40, 2554-2555. (b) Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1986, 108, 303-304.
13. 3SnH with silicon hydrides, see: (a) Itoi, K. Fr. Patent 1,368,522, 1964. Itoi, K.; Kumano, S. Kogyo Kagaku Zasshi 1967, 70, 82-86. (b) Hayashi, K.; Iyoda, J.; Shiihara, I. J. Organomet. Chem. 1967, 10, 81-94. Bellegarde, B.; Pereyre, M.; Valade, J. Bull. Soc. Chim. Fr. 1967, 3082-3083.
14. 3SnH with silicon hydrides, see: (a) Itoi, K. Fr. Patent 1,368,522, 1964. Itoi, K.; Kumano, S. Kogyo Kagaku Zasshi 1967, 70, 82-86. (b) Hayashi, K.; Iyoda, J.; Shiihara, I. J. Organomet. Chem. 1967, 10, 81-94. Bellegarde, B.; Pereyre, M.; Valade, J. Bull. Soc. Chim. Fr. 1967, 3082-3083.
15. 3SnH with silicon hydrides, see: (a) Itoi, K. Fr. Patent 1,368,522, 1964. Itoi, K.; Kumano, S. Kogyo Kagaku Zasshi 1967, 70, 82-86. (b) Hayashi, K.; Iyoda, J.; Shiihara, I. J. Organomet. Chem. 1967, 10, 81-94. Bellegarde, B.; Pereyre, M.; Valade, J. Bull. Soc. Chim. Fr. 1967, 3082-3083.
16. 3SnH with silicon hydrides, see: (a) Itoi, K. Fr. Patent 1,368,522, 1964. Itoi, K.; Kumano, S. Kogyo Kagaku Zasshi 1967, 70, 82-86. (b) Hayashi, K.; Iyoda, J.; Shiihara, I. J. Organomet. Chem. 1967, 10, 81-94. Bellegarde, B.; Pereyre, M.; Valade, J. Bull. Soc. Chim. Fr. 1967, 3082-3083.
17. For catalytic processes, see: (a) Nitzsche, S.; Wick, M. Angew. Chem. 1957, 69, 96. (b) Lipowitz, J.; Bowman, S. A. Aldrichimica Acta 1973, 6, 1-6. (c) Hays, D. S.; Fu, G. C. J. Org. Chem. 1996, 61, 4-5. (d) Hays, D. S.; Scholl, M.; Fu, G. C. J. Org. Chem. 1996, 61, 6751-6752. (e) Lopez, R. M.; Hays, D. S.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 6949-6950.
18. For catalytic processes, see: (a) Nitzsche, S.; Wick, M. Angew. Chem. 1957, 69, 96. (b) Lipowitz, J.; Bowman, S. A. Aldrichimica Acta 1973, 6, 1-6. (c) Hays, D. S.; Fu, G. C. J. Org. Chem. 1996, 61, 4-5. (d) Hays, D. S.; Scholl, M.; Fu, G. C. J. Org. Chem. 1996, 61, 6751-6752. (e) Lopez, R. M.; Hays, D. S.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 6949-6950.
19. For catalytic processes, see: (a) Nitzsche, S.; Wick, M. Angew. Chem. 1957, 69, 96. (b) Lipowitz, J.; Bowman, S. A. Aldrichimica Acta 1973, 6, 1-6. (c) Hays, D. S.; Fu, G. C. J. Org. Chem. 1996, 61, 4-5. (d) Hays, D. S.; Scholl, M.; Fu, G. C. J. Org. Chem. 1996, 61, 6751-6752. (e) Lopez, R. M.; Hays, D. S.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 6949-6950.
20. For catalytic processes, see: (a) Nitzsche, S.; Wick, M. Angew. Chem. 1957, 69, 96. (b) Lipowitz, J.; Bowman, S. A. Aldrichimica Acta 1973, 6, 1-6. (c) Hays, D. S.; Fu, G. C. J. Org. Chem. 1996, 61, 4-5. (d) Hays, D. S.; Scholl, M.; Fu, G. C. J. Org. Chem. 1996, 61, 6751-6752. (e) Lopez, R. M.; Hays, D. S.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 6949-6950.
21. For catalytic processes, see: (a) Nitzsche, S.; Wick, M. Angew. Chem. 1957, 69, 96. (b) Lipowitz, J.; Bowman, S. A. Aldrichimica Acta 1973, 6, 1-6. (c) Hays, D. S.; Fu, G. C. J. Org. Chem. 1996, 61, 4-5. (d) Hays, D. S.; Scholl, M.; Fu, G. C. J. Org. Chem. 1996, 61, 6751-6752. (e) Lopez, R. M.; Hays, D. S.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 6949-6950.
22. Kula, M.-R.; Lorberth, J.; Amberger, E. Chem. Ber. 1964, 97, 2087-2089; Chem. Abstr. 1964, 61, 7035g.
23. Kula, M.-R.; Lorberth, J.; Amberger, E. Chem. Ber. 1964, 97, 2087-2089; Chem. Abstr. 1964, 61, 7035g.
24. For example, see: (a) Colvin, E. W. Silicon in Organic Synthesis; Butterworth: Boston, 1981. (b) Fleck, T. J. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995; pp 4028-4029.
25. For example, see: (a) Colvin, E. W. Silicon in Organic Synthesis; Butterworth: Boston, 1981. (b) Fleck, T. J. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995; pp 4028-4029.
26. Jones, K.; Lappert, M. F. J. Organomet. Chem. 1965, 3, 295-307.
27. Neumann, W. P.; Schneider, B.; Sommer, R. Liebigs Ann. Chem. 1966, 692, 1-11.
28. Sommer, R.; Neumann, W. P.; Schneider, B. Tetrahedron Lett. 1964, 3875-3878.
29. 3SnH is proposed to be an intermediate in this reaction, although it was not observed. Creemers, H. M. J. C. Ph.D. Dissertation, University of Utrecht, 1967.
30. 3 is the major (>90%) tin-containing product.
31. 3SnH in 88% yield.
32. 3.
33. Pijselman, J.; Pereyre, M. J. Organomet. Chem. 1973, 63, 139-157.